Asymmetric additions of allyl groups and enolates to the carbonyl (C═O) group of aldehydes and to the C═N group of related electrophilic compounds remains one of the most important and fundamental carbonyl addition reactions for the synthesis of optically active chiral compounds containing a chiral carbon center bonded to an oxygen or nitrogen atom. Such compounds may have utility, for example, as pharmaceutically active compounds, or may be used to prepare other pharmaceutically active compounds. Many highly enantioselective allylation reagents and catalysts have been developed, as described, for example, in Brown, H. C. and Jadhav, P. K., J. Am. Chem. Soc., Vol. 105 (1983), p. 2092; Jadhav, P. K., Bhat, K. S., Perumal P. T. and Brown, H. C., J. Org. Chem., Vol. 51 (1986), p. 432; Racherla, U. S. and Brown, H. C., J. Org. Chem., Vol. 56 (1991), p. 401; Roush, W. R., Walts, A. E. and Hoong, L. K., J. Am. Chem. Soc., Vol. 107 (1985), p. 8186; Roush, W. R. and Banfi, W. L., J. Am. Chem. Soc., Vol. 110 (1988), p. 3979; Hafner, A., Duthaler R. O., Marti, R., Ribs, G., Rothe-Streit, P. and Schwarzenbach, F., J. Am. Chem. Soc., Vol. 114 (1992), p. 2321; Wang, Z., Wang, D. and Sui, X., Chem. Commun. (1996), p. 2261; Wang, D., Wang, Z. G., Wang, M. W., Chen, Y. J., Liu, L. and Zhu, Y., Tetrahedron: Asymmetry, Vol. 10 (1999), p. 327; Zhang, L. C., Sakurai, H. and Kira, M., Chem. Lett. (1997), p. 129. Similarly, highly enantioselective enolate reagents have been developed, as described, for example, in Paterson, I., Lister, M. A. and McClure, C. K., Tetrahedron Lett., vol. 27, (1986), p. 4787; Paterson, I. and Goodman, J. M., Tetrahedron Lett., vol. 30, (1989), p. 997; Paterson, I.,Goodman, J. M., Lister, M. A., Schumann, R. C., McClure, C. K. and Norcross, R. D., Tetrahedron, Vol. 46, (1990), p. 4663; and Cowden, C. J. and Paterson, I., Org. React. Vol. 51, (1997), p. 1.
However, several problems have been found to be associated with the allylation and enolate reagents and catalysts of the prior art, including the expense of preparation, the instability of the reagents or the catalysts, the need for using the reagents or the catalysts in situ or shortly after their preparation, the toxicity of the reagents and the byproducts of the reactions of the reagents and the catalysts with aldehydes, and the ease of separation and purification of the reaction products. A generally applicable method for the allylation and the addition of enolates to aldehydes and related electrophilic compounds requires easily and inexpensively formed, stable, and storable reagents and catalysts, reagents and byproducts having little or no toxicity, and easy separation and purification of the products formed. A method combining all these characteristics has until now proven elusive.